Reduction, Mannich reaction, and antimicrobial activity evaluation of some new 1,2,4-triazol-3-one derivatives

Alpay Karaoğlu, Şengül; DEMİRBAŞ, Ahmet; BEKTAŞ, Hakan; BAŞOĞLU, Serap; YOLAL, Meltem; Fandaklı, Seda

Reduction, Mannich reaction, and antimicrobial activity evaluation of some new 1,2,4-triazol-3-one derivatives

Seda FANDAKLI, (Karadeniz Teknik Üniversitesi, Fen Fakültesi, Kimya Bölümü, Giresun, Türkiye)

Serap BAŞOĞLU, (Karadeniz Teknik Üniversitesi, Fen Fakültesi, Kimya Bölümü, Giresun, Türkiye)

Hakan BEKTAŞ, (Giresun Üniversitesi, Fen Fakültesi, Kimya Bölümü, Giresun, Türkiye)

Meltem YOLAL, (Karadeniz Teknik Üniversitesi, Fen Fakültesi, Kimya Bölümü, Giresun, Türkiye)

Ahmet DEMİRBAŞ, (Karadeniz Teknik Üniversitesi, Fen Fakültesi, Kimya Bölümü, Giresun, Türkiye)

ŞENGÜL ALPAY KARAOĞLU (Rize Üniversitesi, Fen Edebiyat Fakültesi, Biyoloji Bölümü, Rize, Türkiye)

Turkish Journal of Chemistry

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Yıl: 2012 Cilt: 36 Sayı: 4 Sayfa Aralığı: 567 - 582 Metin Dili: İngilizce İndeks Tarihi: 29-07-2022

Reduction, Mannich reaction, and antimicrobial activity evaluation of some new 1,2,4-triazol-3-one derivatives

Öz:

Ethyl[4-arylmethyleneamino-3-(4-metylphenyl)-5-oxo-4,5-dihydro-1H -1,2,4-triazole-1-yl]acetates (3a-e and 10a-d) were obtained starting from 4-amino-2,4-dihydro-3H -1,2,4-triazol-3-ones (1 and 9) in 2 steps. The treatment of 3a-e with NaBH4 resulted in the formation of 3 kinds of product incorporating carboxcilic acid (4a-c) or alcohol (5a-e) functionality. [4-{[(4-Methoxyphenyl)methylene]amino}- and 4-{[pyridin-4- ylmethylene]amino}-3-(4-methylphenyl)-5-oxo-4,5-dihydro-1H -1,2,4-triazole-1-yl] acetic acids (6a, 6e) were obtained by the hydrolysis of the corresponding esters (5a-5e). The treatment of 6a with NaBH4 caused the reduction of only the imine bond; the carboxyl group remained unchanged. Then this carboxylic acid was converted to the corresponding hydrazide (8) in 2 steps by reaction with ethanol and hydrazine hydrate, respectively. The synthesis of Mannich bases was performed by the reaction of the corresponding 1,2,4- triazoles containing an imine group (10a-d) with several primary or secondary amines including morpholine or piperazine nucleus. All newly synthesized compounds were screened for their antimicrobial activity. The antimicrobial activity study revealed that the Mannich bases (11-16) showed good activity against the test microorganisms as compared with ampicillin.

Anahtar Kelime:

Konular: Mühendislik, Kimya

Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık

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APA	Fandaklı S, BAŞOĞLU S, BEKTAŞ H, YOLAL M, DEMİRBAŞ A, Alpay Karaoğlu Ş (2012). Reduction, Mannich reaction, and antimicrobial activity evaluation of some new 1,2,4-triazol-3-one derivatives. , 567 - 582.
Chicago	Fandaklı Seda,BAŞOĞLU Serap,BEKTAŞ Hakan,YOLAL Meltem,DEMİRBAŞ Ahmet,Alpay Karaoğlu Şengül Reduction, Mannich reaction, and antimicrobial activity evaluation of some new 1,2,4-triazol-3-one derivatives. (2012): 567 - 582.
MLA	Fandaklı Seda,BAŞOĞLU Serap,BEKTAŞ Hakan,YOLAL Meltem,DEMİRBAŞ Ahmet,Alpay Karaoğlu Şengül Reduction, Mannich reaction, and antimicrobial activity evaluation of some new 1,2,4-triazol-3-one derivatives. , 2012, ss.567 - 582.
AMA	Fandaklı S,BAŞOĞLU S,BEKTAŞ H,YOLAL M,DEMİRBAŞ A,Alpay Karaoğlu Ş Reduction, Mannich reaction, and antimicrobial activity evaluation of some new 1,2,4-triazol-3-one derivatives. . 2012; 567 - 582.
Vancouver	Fandaklı S,BAŞOĞLU S,BEKTAŞ H,YOLAL M,DEMİRBAŞ A,Alpay Karaoğlu Ş Reduction, Mannich reaction, and antimicrobial activity evaluation of some new 1,2,4-triazol-3-one derivatives. . 2012; 567 - 582.
IEEE	Fandaklı S,BAŞOĞLU S,BEKTAŞ H,YOLAL M,DEMİRBAŞ A,Alpay Karaoğlu Ş "Reduction, Mannich reaction, and antimicrobial activity evaluation of some new 1,2,4-triazol-3-one derivatives." , ss.567 - 582, 2012.
ISNAD	Fandaklı, Seda vd. "Reduction, Mannich reaction, and antimicrobial activity evaluation of some new 1,2,4-triazol-3-one derivatives". (2012), 567-582.

APA	Fandaklı S, BAŞOĞLU S, BEKTAŞ H, YOLAL M, DEMİRBAŞ A, Alpay Karaoğlu Ş (2012). Reduction, Mannich reaction, and antimicrobial activity evaluation of some new 1,2,4-triazol-3-one derivatives. Turkish Journal of Chemistry, 36(4), 567 - 582.
Chicago	Fandaklı Seda,BAŞOĞLU Serap,BEKTAŞ Hakan,YOLAL Meltem,DEMİRBAŞ Ahmet,Alpay Karaoğlu Şengül Reduction, Mannich reaction, and antimicrobial activity evaluation of some new 1,2,4-triazol-3-one derivatives. Turkish Journal of Chemistry 36, no.4 (2012): 567 - 582.
MLA	Fandaklı Seda,BAŞOĞLU Serap,BEKTAŞ Hakan,YOLAL Meltem,DEMİRBAŞ Ahmet,Alpay Karaoğlu Şengül Reduction, Mannich reaction, and antimicrobial activity evaluation of some new 1,2,4-triazol-3-one derivatives. Turkish Journal of Chemistry, vol.36, no.4, 2012, ss.567 - 582.
AMA	Fandaklı S,BAŞOĞLU S,BEKTAŞ H,YOLAL M,DEMİRBAŞ A,Alpay Karaoğlu Ş Reduction, Mannich reaction, and antimicrobial activity evaluation of some new 1,2,4-triazol-3-one derivatives. Turkish Journal of Chemistry. 2012; 36(4): 567 - 582.
Vancouver	Fandaklı S,BAŞOĞLU S,BEKTAŞ H,YOLAL M,DEMİRBAŞ A,Alpay Karaoğlu Ş Reduction, Mannich reaction, and antimicrobial activity evaluation of some new 1,2,4-triazol-3-one derivatives. Turkish Journal of Chemistry. 2012; 36(4): 567 - 582.
IEEE	Fandaklı S,BAŞOĞLU S,BEKTAŞ H,YOLAL M,DEMİRBAŞ A,Alpay Karaoğlu Ş "Reduction, Mannich reaction, and antimicrobial activity evaluation of some new 1,2,4-triazol-3-one derivatives." Turkish Journal of Chemistry, 36, ss.567 - 582, 2012.
ISNAD	Fandaklı, Seda vd. "Reduction, Mannich reaction, and antimicrobial activity evaluation of some new 1,2,4-triazol-3-one derivatives". Turkish Journal of Chemistry 36/4 (2012), 567-582.